artemisic acid profile

artemisic acid: isolated from Artemisia annua; MF: C28-H58-O; RN from Toxline [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

(+)-artemisinic acid : A monocarboxylic acid that is prop-2-enoic acid which is substituted at position 2 by a 4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl group (the 1S,4R,4aS,8aR diastereoisomer). It is a sesquiterpenoid precursor of artemisinin, obtained from sweet wormwood, Artemisia annua. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Related Flora

Flora	Rank	Flora Definition	Family	Family Definition
Artemisia	genus	A plant genus of the family ASTERACEAE with strong-smelling foliage. It is a source of SANTONIN and other cytotoxic TERPENES.[MeSH]	Asteraceae	A large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH]

ID Source	ID
PubMed CID	10922465
CHEMBL ID	457385
CHEBI ID	63749
SCHEMBL ID	159983
MeSH ID	M0137692

Synonym
artemisinic acid
artemisic acid
222F86B0-6F56-4D85-98B2-F1B0E146A747
CHEMBL457385
chebi:63749 ,
C20309
S9135
unii-53n99527g7
1-naphthaleneacetic acid, 1,2,3,4,4a,5,6,8a-octahydro-4,7-dimethyl-alpha-methylene-, (1r-(1alpha,4beta,4abeta,8abeta))-
2-((1r,4r,4as,8ar)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)prop-2-enoic acid
ec 617-040-5
53n99527g7 ,
80286-58-4
2-[(1r,4r,4as,8ar)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoic acid
(+)-artemisinic acid
1-naphthaleneacetic acid, 1,2,3,4,4a,5,6,8a-octahydro-4,7-dimethyl-.alpha.-methylene-, (1r-(1.alpha.,4.beta.,4a.beta.,8a.beta.))-
singleex artemisinic acid
qing hao acid
artemisinic acid [inci]
qing hau acid
artemisininic acid
arteannuic acid
1-naphthaleneacetic acid, 1,2,3,4,4a,5,6,8a-octahydro-4,7-dimethyl-.alpha.-methylene-, (1r,4r,4as,8ar)-
AKOS017343176
LMPR0103190015
SCHEMBL159983
artemisinic-acid
2-((1r,4r,4as,8ar)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)acrylic acid
PLQMEXSCSAIXGB-SAXRGWBVSA-N
mfcd00238540
Q27132774
4,11(13)-amorphadien-12-oic acid
4,11(13)-cadinadien-12-oic acid
qing hao acid; artemisinic acid; arteannuic acid
HY-N1984
CS-0018305
CCG-266821
4,11(13)-cadinadien-12-oic acid;artemisic acid
A856098
AC-34595
AS-78501
artemisinicacid
2-[(1r,4r,4as,8ar)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoicacid

Role	Description
metabolite	Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
monocarboxylic acid	An oxoacid containing a single carboxy group.
carbobicyclic compound	A bicyclic compound in which all the ring atoms are carbon.
sesquiterpenoid	Any terpenoid derived from a sesquiterpene. The term includes compounds in which the C15 skeleton of the parent sesquiterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).
octahydronaphthalenes	Any carbobycyclic compound that is an octahydronaphthalene or a compound obtained from an octahydronaphthalene by formal substitution of one or more hydrogens.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Assay ID	Title	Year	Journal	Article
AID338835	Cytotoxicity against mouse EAC after 3 days by MTT assay	1993	Journal of natural products, Jun, Volume: 56, Issue:6	Cytotoxicity of artemisinin-related endoperoxides to Ehrlich ascites tumor cells.
AID338837	Cytotoxicity against mouse EAC at >175 uM after 3 days by MTT assay	1993	Journal of natural products, Jun, Volume: 56, Issue:6	Cytotoxicity of artemisinin-related endoperoxides to Ehrlich ascites tumor cells.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (1.67)	18.7374
1990's	5 (8.33)	18.2507
2000's	11 (18.33)	29.6817
2010's	38 (63.33)	24.3611
2020's	5 (8.33)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	4 (6.56%)	6.00%
Case Studies	1 (1.64%)	4.05%
Observational	0 (0.00%)	0.25%
Other	56 (91.80%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	2.05	1	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	2.13	1	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	2.21	1	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
isopentenyl pyrophosphate isopentenyl pyrophosphate: substrate for isopentenyl pyrophosphate isomerase; RN given refers to unlabeled cpd; a nonpeptide mycobacterial antigen that stimulates gamma delta T cells. isopentenyl diphosphate : A prenol phosphate comprising 3-methylbut-3-en-1-ol having an O-diphosphate substituent.	2.1	1	prenol phosphate	antigen; antioxidant; epitope; Escherichia coli metabolite; mouse metabolite; phosphoantigen
chloroquine Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.	2.43	2	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
galactose galactopyranose : The pyranose form of galactose.	2.21	1	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	2.48	2	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
ascaridole ascaridole: monoterpene endoperoxide with anthelmintic properties; structure given in first source. ascaridole : A p-menthane monoterpenoid that is p-menth-2-ene with a peroxy group across position 1 to 4.	1.98	1	organic heterobicyclic compound; organic peroxide; p-menthane monoterpenoid	antileishmanial agent; antinematodal drug; plant metabolite
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.06	1	benzenes; phenyl acetates
alkenes [no description available]	2.6	1
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	2.25	1	pseudohalide anion	mitochondrial respiratory-chain inhibitor
substance p [no description available]	2.41	1	peptide	neurokinin-1 receptor agonist; neurotransmitter; vasodilator agent
artemisinin (+)-artemisinin : A sesquiterpene lactone obtained from sweet wormwood, Artemisia annua, which is used as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria.	12.55	27	organic peroxide; sesquiterpene lactone	antimalarial; plant metabolite
artemether Artemether: An artemisinin derivative that is used in the treatment of MALARIA.. artemether : An artemisinin derivative that is artemisinin in which the lactone has been converted to the corresponding lactol methyl ether. It is used in combination with lumefantrine as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria.	1.98	1	artemisinin derivative; cyclic acetal; organic peroxide; semisynthetic derivative; sesquiterpenoid	antimalarial
diazene [no description available]	2.1	1	nitrogen hydride
singlet oxygen Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.	2.77	3	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
mevalonic acid Mevalonic Acid: A dihydroxy monocarboxylic acid and precursor in the biosynthetic pathway known as the mevalonate pathway, which produces terpenes and steroids that are vital for diverse cellular functions.. mevalonic acid : A racemate composed of equimolar amounts of (R)- and (S)-mevalonic acid.. (R)-mevalonic acid : The (R)-enantiomer of mevalonic acid.	2.03	1	3,5-dihydroxy-3-methylpentanoic acid
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	2.13	1	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	2.07	1	cinnamic acid	plant metabolite
glycosides [no description available]	2.07	1
squalene Addavax: an oil-water nanoemulsion and adjuvant containing squalene, Tween 80, and sorbitane trioleate	2.06	1	triterpene	human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
sesquiterpenes [no description available]	5.83	17
artemotil artemotil: structure given in first source; RN given refers to cpd without isomeric designation	1.98	1	artemisinin derivative
scopoletin [no description available]	8.44	2	hydroxycoumarin	plant growth regulator; plant metabolite
jasmonic acid jasmonic acid: a derivative of alpha-linolenic acid that has a role in plant response to herbivory analogous to the role of prostanoids in inflammation in mammals;. jasmonic acid : An oxo monocarboxylic acid that is (3-oxocyclopentyl)acetic acid substituted by a (2Z)-pent-2-en-1-yl group at position 2 of the cyclopentane ring.	2.1	1	oxo monocarboxylic acid	jasmonates; plant metabolite
eupatoriopicrine [no description available]	1.98	1	germacranolide
9,12,13-trihydroxy-10-octadecenoic acid 9,12,13-trihydroxy-10-octadecenoic acid: from roots & stem of Glycyrrhiza glabara; antistress compound; RN refers to (E)-isomer. 9,12,13-trihydroxyoctadec-10-enoic acid : A TriHOME that is octadec-10-enoic acid in which the three hydroxy substituents are located at positions 9, 12 and 13.	2.07	1
caryophyllene caryophyllene: RN given refers to cpd without isomeric designation; structure given in first source	2.06	1
germacrene d germacrene D: RN in 9th CI Form Index for unspecified stereoisomer: 37839-63-7	2.06	1
beta-escin [no description available]	2.08	1
arteannuin b [no description available]	9.69	10
artenimol artenimol: derivative of antimalarial drug artemisinin (quinghaosu)	1.98	1
artemisitene artemisitene: RN given for (3R-(3alpha,5abeta,6beta,8abeta,12beta,12aR*))-isomer; structure in first source	2.08	1
dihydroartemisinic acid dihydroartemisinic acid: structure in first source. dihydroartemisinic acid : A monocarboxylic acid that is propanoic acid substituted at position 2 by a (1S,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl group. It is a sesquiterpenoid precursor of the antimalarial drug, artemisinin.	3.78	10	carbobicyclic compound; monocarboxylic acid; octahydronaphthalenes; sesquiterpenoid	plant metabolite
amorpha-4,11-diene amorpha-4,11-diene: a precursor to the antimalarial drug artemisinin	3.84	3	octahydronaphthalenes; sesquiterpene
vindoline [no description available]	2.1	1
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2.08	1	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
methyl jasmonate [no description available]	2.06	1
sodium artesunate [no description available]	1.98	1

Condition	Relationship Strength	Studies
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	1.98	1
Autoimmune Urticaria [description not available]	4.02	9
Anaphylactic Reaction [description not available]	4.02	9
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	4.02	9
Anaphylaxis An acute hypersensitivity reaction due to exposure to a previously encountered ANTIGEN. The reaction may include rapidly progressing URTICARIA, respiratory distress, vascular collapse, systemic SHOCK, and death.	4.02	9
Infections, Plasmodium [description not available]	2.47	2
Malaria A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.	2.47	2
Plasmodium falciparum Malaria [description not available]	2.46	2
Malaria, Falciparum Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.	2.46	2
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.76	3
Insulin Sensitivity [description not available]	2.07	1
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	2.07	1
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	2.07	1
Leukemia P388 An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.	1.98	1
Cancer of Liver [description not available]	1.98	1
Cancer of Stomach [description not available]	1.98	1
Liver Neoplasms Tumors or cancer of the LIVER.	1.98	1
Stomach Neoplasms Tumors or cancer of the STOMACH.	1.98	1

artemisic acid

Description

Cross-References

Synonyms (43)

Roles (1)

Drug Classes (4)

Bioassays (2)

Research

Studies (60)

Market Indicators

Research Demand Index: 30.93

Study Types